Pentadecanols are well known in commerce as components of a variety of commercially available fatty alcohol blends. These blends generally consist of fatty alcohols spanning a range of molecular weights. For example, NEODOL® 45 contains mainly alcohols with 14 or 15 carbons; NEODOL 25 contains mainly alcohols with 12, 13, 14, or 15 carbons.
Normal 1-pentadecanol is well known as a fragrance and flavoring ingredient as well as a skin emollient ingredient. It is most commonly obtained by extraction from vegetable materials. For example, it can be obtained from a CO2 extract of angelica seed oil. It can also be obtained from hydrodistilled oil obtained from the stem bark of Myrica esculenta Buch. Ham. ex D. Don (Nat Prod Res. 2012; 26(23):2266-9). It is known to have specific activity against Proponibacterium acnes (Journal of Natural Products Vol. 57, No. 1, pp. 9-17, January 1994) and can be used as a topical treatment for acne vulgaris (U.S. Pat. No. 5,380,763). Its extraction from vegetable sources limits availability and results in high cost.
A second type of primary pentadecanol is produced by performing the oxo hydroformylation reaction on a linear tetradecene as disclosed in U.S. Pat. No. 7,183,446. This yields a pentadecanol mixture containing 40% or greater of branched species. While this route provides better availability and reduced cost, it yields branched species that may have undesirable properties in some applications if substituted for normal 1-pentadecanol. If this type of pentadecanol is used as a skin emollient or to synthesize useful derivatives like surface active agents, the high degree of branching may limit its functionality in these uses. There is a need for a pentadecanol with a lower proportion of branched species that can be produced in volume and at reasonable cost.